Osano Mana, Jhaveri Dishit P, Wipf Peter
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashimita, Tama-ku, Kawasaki 214-8571, Japan.
Org Lett. 2020 Mar 20;22(6):2215-2219. doi: 10.1021/acs.orglett.0c00417. Epub 2020 Feb 27.
A new variant of the intramolecular Diels-Alder oxazole (IMDAO) cycloaddition that provides direct access to 6-azaindoles was developed. The IMDAO reaction was applied in a total synthesis of the aminophenylpyrrole-derived alkaloid marinoquinoline A, also featuring the use of a Curtius reaction for preparation of a 5-aminooxazole, a propargylic C,H-bond insertion, an alkyne-allene isomerization, and a ruthenium-catalyzed cycloisomerization for benzene ring annulation to the 6-azaindole.
开发了一种分子内Diels-Alder恶唑（IMDAO）环加成反应的新变体，该变体可直接合成6-氮杂吲哚。IMDAO反应被应用于氨基苯基吡咯衍生生物碱马里诺喹啉A的全合成中，该合成还包括使用库尔提斯反应制备5-氨基恶唑、炔丙基C-H键插入、炔-丙二烯异构化以及钌催化的环异构化反应，用于将苯环环合到6-氮杂吲哚上。
